九元氮杂环化合物合成最新研究进展

doi:10.6023/cjoc202206035

摘要/Abstract

九元氮杂环骨架广泛存在于天然产物和生物活性分子中, 其环系的刚性结构对这类分子的生物活性及药理活性的调控具有重要的作用, 是被广泛关注的中环化合物之一. 由于九元环的熵和环张力的增加, 其合成往往是有机合成中的难点, 特别是环上取代基立体化学的有效控制更是极大挑战之一. 综述了近年来九元氮杂环化合物合成的新策略和新方法, 以及这些策略和方法在合成含九元氮杂环骨架天然产物和药物分子中的应用.

关键词: 九元氮杂环, 中环化合物, 环化反应, 环加成反应, 扩环反应

Nine-membered N-heterocycle scaffolds are widely found in natural products and biologically active molecules. The rigid structure of the medium-sized ring plays important roles in the regulation of their biological and pharmacological activities. Therefore, nine-membered N-heterocycle is one of the most attractive medium-sized ring compounds. Because of the increasing entropy and ring extension of nine-membered ring skeleton, the synthesis of nine-membered N-heterocycles is still difficult; especially the effective control of substituent stereoselectivity for the nine-membered ring is one of the greatest challenging topics This review summarizes the novel synthetic strategies of nine-membered N-heterocycles and their applications in the synthesis of natural products and pharmaceutically active molecules containing nine-membered ring scaffold in recent years.

Key words: nine-membered N-heterocycles, medium-sized ring compounds, cyclization, cycloaddition, ring expansion

引用此文

覃小婷, 邹宁, 农彩梅, 莫冬亮. 九元氮杂环化合物合成最新研究进展[J]. 有机化学, 2023, 43(1): 130-155.

Xiaoting Qin, Ning Zou, Caimei Nong, Dongliang Mo. Recent Advances on the Synthesis of Nine-Membered N-Heterocycles[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 130-155.

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图/表 50

图1. 一些含九元氮杂环骨架的天然产物

Figure 1. Some natural products containing nine-membered N- heterocyclic skeleton

图式1. 分子内Heck环化反应合成九元氮杂环化合物

Scheme 1. Intramolecular Heck cyclization to synthesize nine- membered N-heterocycles

图式2. 分子间Ugi反应和氢芳基化环化构建九元氮杂环化合物

Scheme 2. Intermolecular Ugi reaction/hydroarylation to form nine-membered N-heterocycles

图式3. 醛亚胺缩合/1,6-HT/Mannich环化级联反应构建多环吲哚-3,4-稠合九元环化合物

Scheme 3. Aldimine condensation/1,6-HT/Mannich/cyclization cascade to construct polycyclic indole-3,4-fused nine-membered rings

图式4. 醛亚胺缩合/1,6-HT/Mannich级联反应构建多环吲哚- 3,4-稠合九元环化合物的机理

Scheme 4. Mechanism of aldimine condensation/1,6-HT/Man- nich cascade to synthesize polycyclic indole-3,4-fused nine- membered ring

图式5. 铁催化炔烃-羰基复分解合成6,7-二氢-5H-二苯并[c,e]氮酮

Scheme 5. Iron(III)-catalyzed alkyne-carbonyl metathesis for the synthesis of 6,7-dihydro-5H-dibenzo[c,e]azonines

图式6. 1,4-重排扩环反应构建九元氮杂环化合物

Scheme 6. 1,4-Rearrangement and ring-expansion for the synthesis of nine-membered N-heterocycles

图式7. 1,4-重排扩环反应构建九元氮杂环化合物的机理

Scheme 7. The mechanism of 1,4-rearrangement and ring-expansion for the synthesis of nine-membered N-heterocycles

图式8. 点击反应/[3,3]-重排构建九元氮杂环化合物

Scheme 8. Click reaction/[3,3]-rearrangement to construct nine-membered N-heterocycles

图式9. 氢烷氧基化/克莱森重排构建九元氮杂环化合物

Scheme 9. Construction of nine-membered N-heterocycles by hydroalkoxylation/Claisen rearrangement

图式10. 氢烷氧基化/克莱森重排构建九元氮杂环化合物反应机理

Scheme 10. Mechanism of the construction of nine-membered N-heterocycles by hydroalkoxylation/Claisen rearrangement

图式11. 去质子/迁移扩环反应构建苯并九元氮杂环化合物

Scheme 11. Construction of benzo-nine-membered N-hetero- cycles by deprotonation/migration and ring expansion

图式12. 铱催化不对称烯丙基化去芳构化/Mannich/水解级联反应合成吲哚稠合中环化合物

Scheme 12. Iridium-catalyzed asymmetric allylation dearomati- zation/Mannich/hydrolysis cascade reaction to synthesize indole- fused medium-sized-ring compounds

图式13. 氧化去芳构化/扩环反应构建九元氮杂环化合物

Scheme 13. Construction of nine-membered N-heterocycles by tandem oxidation dearomatization and ring-expansion

图式14. 电化学合成苯并九元氮杂环化合物

Scheme 14. Electrochemical synthesis of benzo-nine-membered N-heterocycles

图式15. 溴化扩环反应不对称构建九元氮杂环化合物

Scheme 15. Construction of nine-membered N-heterocycles by asymmetric bromination and ring-expansion

图式16. [6+3]环加成构建桥环九元氮杂环化合物机理

Scheme 16. Proposed mechanism for the formation of bridged nine-membered N-heterocycles by [6+3] cycloaddition

图式17. [5+4]环加成构建苯并呋喃氮杂九元环化合物

Scheme 17. Construction of benzofuran-fused nine-membered N-heterocycles by [5+4] cycloaddition

图式18. 不对称[5+4]环加成反应构建苯并呋喃氮杂九元环化合物

Scheme 18. Construction of benzofuran-fused nine-membered N-heterocycles by asymmetric [5+4] cycloaddition reaction

图式19. Pd催化不对称[5+4]环加成构建九元氮杂环化合物

Scheme 19. Pd-catalyzed asymmetric [5+4] cycloaddition to form nine-membered N-heterocycles

图式20. Pd催化双脱羧扩环反应构建三氟甲基取代的九元氮杂环化合物

Scheme 20. Palladium-catalyzed double-decarboxylative ring-expansion reaction to construct trifluoromethyl substituted nine-mem- bered N-heterocycles

图式21. Pd催化[5+4]环加成构建含二氟取代的九元氮杂内酯化合物

Scheme 21. Pd-catalyzed [5+4] cycloaddition to form nine-membered N-heterocycles containing difluoro group

图式22. Pd(0)/Rh(II)协同催化[6+3]环加成反应构建九元氮杂环化合物

Scheme 22. Synergistic Pd(0)/Rh(II) dual catalytic [6+3] cycloaddition for the synthesis of nine-membered N-heterocycles

图式23. Pd(0)催化[6+3]环加成反应构建九元氮杂环化合物

Scheme 23. Pd(0)-catalyzed [6+3] cycloaddition for the construction of nine-membered N-heterocycles

图式24. [3+2]环加成[3,3]重排构建九元氮杂环化合物

Scheme 24. [3+2] cycloaddition and [3,3]-rearrangement to form nine-membered N-heterocycles

图式25. [3+2]环加成[3,3]重排构建九元氮杂环反应机理

Scheme 25. Mechanism for [3+2] cycloaddition of [3,3]-rearrangement to form nine-membered N-heterocycles

图式26. [3+2]环加成/[3,3]重排构建氮杂九元环化合物

Scheme 26. Construction of nine-membered N-heterocycles by [3+2] cycloaddition/[3,3]-rearrangement

图式27. 铁(III)/铜(II)-共催化环加成/[3,3]重排/N—O键裂解级联反应合成多取代吡咯嗪

Scheme 27. Iron(III)/copper(II)-cocatalyzed cycloaddition/[3,3]-rearrangement/N—O bond cleavage cascade reaction for the synthesis of polysubstituted pyrrolizines

图式28. 铜催化九元氮杂环的动力学拆分

Scheme 28. Copper-catalyzed kinetic resolution of nine-membered N-heterocycles

表1. Yb(OTf)3催化环加成重排构建氮杂九元环化合物

Table 1. Yb(OTf)3 catalyzed cycloaddition and rearrangement to form nine-membered N-heterocycles

图式29. Yb(OTf)3和可以光接力催化构建氮杂九元环内过氧化化合物

Scheme 29. Yb(OTf)3 and visible light relay catalyzed construction of aza-nine-membered endoperoxides

图式30. AgNO3催化环加成/重排构建手性九元氮杂环化合物

Scheme 30. AgNO3 catalyzed cycloaddition/rearrangement to form chiral nine-membered N-heterocycles

图式31. 氢烷氧基化和[4+2]环加成反应构建九元氮杂环化合物

Scheme 31. Hydroalkoxylation and [4+2] cycloaddition to construct nine-membered N-heterocycles

图式32. 卡宾插入和Cope重排构建九元氮杂环化合物

Scheme 32. Insertion of carbene and Cope rearrangement to synthesize nine-membered N-heterocycles

图式33. 卡宾插入和Cope重排构建九元氮杂环化合物的反应机理

Scheme 33. Mechanism for the carbene insertion and Cope rearrangement to construct nine-membered N-heterocycles

图式34. 偶联串联反应构建氮杂九元环化合物

Scheme 34. Coupling cascade reaction to construct nine-membered N-heterocycles

图式35. Ugi多组分反应构建九元氮杂环化合物

Scheme 35. Ugi multicomponent reaction to construct nine-membered N-heterocycles

图式36. C—H活化构建九元氮杂环化合物

Scheme 36. C—H activation for the construction of nine-membered N-heterocycles

图式37. 多组分构建九元氮杂环化合物

Scheme 37. Multi-component construction of nine-membered N-heterocycles

图式38. 多组分串联反应构建九元二氮杂环化合物

Scheme 38. Multi-component cascade construction of nine-membered diazoheterocycles

图式39. 酰化/裂解构建氮杂九元环化合物

Scheme 39. Acylation/cleavage to construct nine-membered N- heterocycles

图式40. 光催化自由基迁移构建九元氮杂环化合物

Scheme 40. Photocatalytic radical shift to construct nine-membered N-heterocycles

图式41. 光催化自由基迁移构建氮杂九元环化合物机理

Scheme 41. Reaction mechanism of photocatalytic radical shift to construct nine-membered N-heterocycles

图式42. 无金属级联环化反应构建九元氮杂环化合物

Scheme 42. Metal-free cascade cyclization for the construction of nine-membered N-heterocycles

图式43. 分子内环化在吲哚内酰胺生物碱全合成中的应用

Scheme 43. Application of intramolecular cyclization in the total synthesis of indole lactam alkaloids

图式44. 分子内胺化反应在生物碱serratine全合成中的应用

Scheme 44. Application of intermolecular amination reaction in the total synthesis of serratine alkaloid

图式45. 分子内Michael加成反应在生物碱(–)-indolactam V 合成中的应用

Scheme 45. Application of intramolecular Michael addition reaction in the total synthesis of natural product (–)-indolatam V

图式46. 分子内缩合在生物碱(–)-Rhazinilam全合成中的应用

Scheme 46. Application of intramolecular condensation in total synthesis of alkaloid (–)-rhazinilam

图式47. 分子内环化在生物碱(±)-Isopalhinine A, (±)-Pal- hinine A, (±)-Palhinine D全合成中的应用

Scheme 47. Application of intramolecular cyclization in the total synthesis of (±)-Isopalhinine A, (±)-Palhinine A, and (±)-Palhinine D

图式48. 分子内亲核取代环化在生物碱huperzine H全合成中的应用

Scheme 48. Application of intramolecular nucleophilic cyclization in the total synthesis of huperzine H

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